2,4-Dichlorobenzyl chloride → HCID 20365307, compound

HRID 1678984Notes

Reaction equation

[OH:1][CH:2](/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[H-].[Na+].Cl[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[Cl:28]>O1CCCC1>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[CH2:20][O:1][CH:2](/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1

Participants

Conditions

Temperature: 25 °C

Procedure

trans-1-[2-Hydroxy-4-phenylbut-3-enyl]imidazole (430 mg.) in 5 ml. dry tetrahydrofuran was treated under nitrogen with stirring with 96 mg. of sodium hydride (56% dispersion in mineral oil) and the mixture heated under reflux for 30 minutes. After cooling in an ice bath the mixture was treated with stirring with 430 mg. of α,2,4-trichlorotoluene in 5 ml. tetrahydrofuran for 30 minutes at 0° C., one hour at 25° C. and overnight under reflux. The resulting mixture was evaporated to dryness, ether (150 ml.) added and the ether extract washed with water, dried over magnesium sulfate and evaporated to afford trans-1-[2-(2,4-dichlorobenzyloxy)-4-phenylbut-3-enyl]imidazole. The nitrate salt precipitated from ether and was crystallized from ethyl acetate, m.p. 133.5°-134.5° C. (foaming).

Workup

temperatureunder reflux for 30 minutes
temperatureAfter cooling in an ice bath the mixture
additionwas treated
stirringwith stirring with 430 mg
customThe resulting mixture was evaporated to dryness, ether (150 ml.)
additionadded
extractionthe ether extract
washwashed with water
dry with materialdried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-055ba549b48843d4b1bdc7bfe5c5f5f5
Source dataset: uspto-grants-1978_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04078071

Reaction notes

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